Hydrochloric Acid → 5-(3-methoxypropoxy)-7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxylic acid
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[C:14]([N:16]([CH3:26])[S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)(=[O:19])=[O:18])[CH:15]=1)[NH:12][C:11]([C:27]([O:29]CC)=[O:28])=[CH:10]2.[OH-].[Na+].C(O)C.Cl>O.O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[C:14]([N:16]([CH3:26])[S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)(=[O:18])=[O:19])[CH:15]=1)[NH:12][C:11]([C:27]([OH:29])=[O:28])=[CH:10]2Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A mixture of ethyl 5-(3-methoxypropoxy)-7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxylate (3.50 g), 1N aqueous sodium hydroxide solution (10 mL), ethanol (10 mL) and tetrahydrofuran (10 mL) was stirred at 50° C. for 1 hr. 1N Hydrochloric acid (10 mL) and water were added to the reaction mixture, and the mixture was extracted with a mixed solvent of tetrahydrofuran-ethyl acetate. The organic layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained crystals were washed with hexane to give the title compound (3.26 g, 100%) as colorless crystals.
Workup
- extractionthe mixture was extracted with a mixed solvent of tetrahydrofuran-ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
- washThe obtained crystals were washed with hexane
Sources & evidence
- ORD record
- ord-b6c564312a3a4df28c8f7067474612fe
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07718798B2
Reaction notes
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